Rupert Legh has a three-pronged attack to finally conquer The Everest

Rupert Legh, one of the nation’s leading racehorse owners, is not giving up on his dream of winning The Everest.

The Melbourne finance guru has had a starter in each of the three runnings so far of the world’s richest turf race but luck has deserted his horses.

But at Royal Randwick on Saturday, Legh is gang-tackling the $15 million The TAB Evererst (1200m) again with three sprinters – Santa Ana Lane, Tofane and Dollar For Dollar.

For good measure, Legh is also in the ownership group of two stayers, Master Of Wine and Chapada, who are in Saturday’s $5 million Caulfield Cup (2400m).



Legh, who can’t be at either track due to the coronavirus pandemic, recalled a mantra instilled in him by his mother many, many years ago when asked if he believed he was overdue for a change of luck in The Everest.

“My mother always said unless you have earned something, you will never have full respect for it,’’ Leg said.

“Nothing beats hard work and persistence.’’

So, Legh is chasing The Everest again.

His first attempt was in 2017 when his champion sprinter Chautauqua, carrying the owner’s now very familiar racing colours of navy blue, gold lightning bolt and gold and white armbands, to an unlucky fourth behind Redzel.

Santa Ana Lane races in the same colours and has contested the last two Everests but luck was against him both times.

Santa Ana Lane was a narrow second to Yes Yes Yes in last year’s The Everest. Picture: AAPSource:AAP

But Santa Ana Lane looked likely to miss a start in The Everest until slot-holder Coolmore swooped late last month.

“It was crazy stuff,’’ Legh said.

“I was thinking why wouldn’t they pick this horse up? This time last year he was rated the number one sprinter in the world.’’

Legh is adamant the ageing sprinter is far from a spent force. After all, Santa Ana Lane has the two fastest Randwick 1200m times of any horse still in training – he ran a then course record 1m 7.45s winning the Premiere Stakes two years ago only to strike an unsuitable heavy track in The Everest when finishing sixth.

Then last year, Santa Ana Lane lowered his own course standard running 1m 7.4s in The Everest, only to finish an unlucky second to Yes Yes Yes who stopped the clock at a scarcely believable 1m 7.32s.

Legh wonders to this day what might have been if Santa Ana Lane wasn’t held up for a run at a vital stage in the straight.

“If you look at the race last year, with any sort of luck he would have won it,’’ Legh said.

“Glen Boss (Yes Yes Yes) put us in a pocket, good riding by him on the winner, he had us where he wanted us on the inside of him.

“Yes Yes Yes got going and put two or three lengths on us and when ‘Santa’ got out and around them, he finished fast and was beaten a half length.

“Two strides past the post he was in front.’’

Chautauqua was unlucky fourth in the inaugural The Everest. Picture: AAPSource:AAP

Santa Ana Lane, trained by Anthony and Sam Freedman, also ran second to Nature Strip in the Group 1 TJ Smith Stakes over the Randwick 1200m course earlier this year.

If Santa Ana Lane, with more than $7.7 million prizemoney already in the bank, can finally win The Everest at his third attempt, he can lift his career earnings to nearly $14 million and third on the all-time list.

Legh’s three sprinters are all going into The Everest after having their final lead-up runs in the Group 2 Gilgai Stakes at Flemington earlier this month where Dollar For Dollar finished a close second, Tofane was fourth and Santa Ana Lane, unsuited by the sit-sprint nature of the race, was a first-up sixth.

Tofane is one of the most improved sprinting mares in training and has been set for The Everest by trainer Mike Moroney since she ran down Pierata in the Group 1 All Aged Stakes at Randwick last April.

Rated a $21 chance in latest TAB Fixed Odds Everest betting alongside Santa Ana Lane, Tofane will be ridden by Tommy Berry who had plenty of success for Legh on Chautauqua.

“Tofane has got stronger and is a more mature with her racing manners,’’ Legh said.

“She has had the perfect preparation and even though she missed a place last start, she had no luck in running. She didn’t have a gut-buster that day so it might play in our favour.’’

Dollar For Dollar ($51) is trained by Tony and Calvin McEvoy and although the veteran sprinter has never won at Group 1 level, he has manage three placings including his second to Everest rival Behemoth in the Sir Rupert Clarke Stakes at Caulfield just prior to his narrow Gilgai Stakes loss.

“We bought Dollar For Dollar as a yearling,’’ Legh revealed.

“He’s in really good form, he’s tough and this is a tough 1200m race. His ideal distance is between 1200m and 1400m. Stranger things have happened in racing.’’

Legh has an interesting back story. His father was a fighter pilot in World War II, his mother was also a pilot, ferrying new fighter jets like Spitfires and Hurricanes, and B52 bombers to RAF bases around England and Europe.

All Aged Stakes winner Tofane is one of Rupert Legh’s three runners in The Everest. Picture: Getty ImagesSource:Getty Images


After the war, Legh’s father enlisted in England’s secretive spy organisation, MI5, and his family lived a nomadic lifestyle, eventually moving to Victoria.

“My father was never at home, my mother brought us up and she was a great influence on me,’’ Legh said.

“In hindsight, I had a great upbringing, I learned about life very quickly.’’

Legh has had a keen interest in racing since his boyhood days when he was boarding with friends in northern Victoria.

“My mother was living in another part of Victoria at the time trying to make a living,’’ he recalled.

“So, I stayed with my best mate and his mother was a mad punter. Every Saturday morning she would have the form guide out and doing her selections for the Daily Double.’’

When Legh turned 17, he joined the Victorian Police. He spent four years in uniform but for a young man in a hurry to get ahead in life, public service wasn’t going to cut it.

“I enjoyed my time with the police but I got out when I was 22,’’ Legh said.

“I was finding it was a job where you didn’t get rewarded for ability. I wanted to get somewhere quickly but I was being held back.’’

Dollar for Dollar was a late addition to The Everest. Picture: Getty ImagesSource:Supplied

This is when Legh made a career choice that would define his life. He found employment in the finance industry.

Just six years later, Legh set up his own finance business.

“It was a massive gamble,’’ he said.

“At the time, my wife and I had two kids, a mortgage on a little house we paid $13,000 for, and no money in the bank.

“I was playing footy at the time (he was a centre half-back or full-back and good enough to have a long career in the VFA with clubs like Caulfield and Prahran) and earning some extra money so that was my security blanket.’’

Legh also took on another job, cleaning bakeries at night to make ends meet.

These were tough times for Legh and his young family.

“We sacrificed a lot,’’ he recalled.

“But I was fortunate to a very special wife, Cheryl, who I went to school with. We got married when Cheryl was 19 and I was 21.

‘’We grew up together and we grew together. She allowed me to work my backside off to get ahead.’’

And all these years later, this is the reason Legh has three runners in The Everest and two in the Caulfield Cup on Saturday – sheer hard work and persistence.

Originally published asLegh’s triple bid to end Everest misfortune

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